AR106299A1 - PIRIDONA COMPOUNDS AND AGRICULTURAL AND HERTICAL FUNGICIDES CONTAINING THESE COMPOUNDS AS ACTIVE INGREDIENT - Google Patents

PIRIDONA COMPOUNDS AND AGRICULTURAL AND HERTICAL FUNGICIDES CONTAINING THESE COMPOUNDS AS ACTIVE INGREDIENT

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AR106299A1
AR106299A1 ARP160103080A ARP160103080A AR106299A1 AR 106299 A1 AR106299 A1 AR 106299A1 AR P160103080 A ARP160103080 A AR P160103080A AR P160103080 A ARP160103080 A AR P160103080A AR 106299 A1 AR106299 A1 AR 106299A1
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group
substituent
optionally substituted
haloalkyl
alkyl
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Nishida Akihiro
Ohara Toshiaki
Yutani Satoshi
Fukumoto Takeshi
Kouno Toshiyuki
Naito Ryohei
Ikishima Hideaki
Umetani Hideki
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Mitsui Chemicals Agro Inc
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    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
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    • C07F7/00Compounds containing elements of Groups 4 or 14 of the Periodic System
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    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N55/00Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
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    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01PBIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
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    • C07D211/84Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
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    • C07D213/60Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D213/04Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62Oxygen or sulfur atoms
    • C07D213/63One oxygen atom
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    • C07D213/02Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D401/04Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07F7/12Organo silicon halides

Abstract

Reivindicación 1: Un compuesto representado por la fórmula (1) o una de sus sales, [caracterizado porque R¹ representa un grupo hidroxi, un grupo ciano, un grupo alquilo C₁₋₆ opcionalmente sustituido con el sustituyente A, un grupo haloalquilo C₁₋₆, un grupo cicloalquilo C₃₋₈ opcionalmente sustituido con el sustituyente A, un grupo alquenilo C₂₋₆ opcionalmente sustituido con el sustituyente A, un grupo haloalquenilo C₂₋₆, un grupo alquinilo C₂₋₆ opcionalmente sustituido con el sustituyente A, un grupo haloalquinilo C₂₋₆, un grupo alcoxi C₁₋₆ opcionalmente sustituido con el sustituyente A, un grupo haloalcoxi C₁₋₆,un grupo cicloalcoxi C₃₋₈ opcionalmente sustituido con el sustituyente A, grupo alquenil C₂₋₆-oxi opcionalmente sustituido con el sustituyente A, un grupo haloalquenil C₂₋₆-oxi, un grupo alquinil C₃₋₆-oxi opcionalmente sustituido con el sustituyente A, un grupo haloalquinil C₃₋₆-oxi, o un R¹⁰R¹¹N- (en donde R¹⁰ y R¹¹ representan cada uno, de modo independiente, un átomo de hidrógeno o un grupo alquilo C₁₋₆); R² representa un átomo de halógeno, un grupo hidroxi, un grupo ciano, un grupo nitro, un grupo alquilo C₁₋₆ opcionalmente sustituido con el sustituyente B, un grupo haloalquilo C₁₋₆, un grupo cicloalquilo C₃₋₈ opcionalmente sustituido con el sustituyente B, un grupo alquenilo C₂₋₆ opcionalmente sustituido con el sustituyente B, un grupo haloalquenilo C₂₋₆, un grupo alquinilo C₂₋₆ opcionalmente sustituido con el sustituyente B, un grupo haloalquinilo C₂₋₆, un grupo alcoxi C₁₋₆ opcionalmente sustituido con el sustituyente B, un grupo haloalcoxi C₁₋₆, un grupo cicloalcoxi C₃₋₈ opcionalmente sustituido con el sustituyente B, un grupo alquenil C₂₋₆-oxi opcionalmente sustituido con el sustituyente B, un grupo haloalquenil C₂₋₆-oxi, un grupo alquinil C₃₋₆-oxi opcionalmente sustituido con el sustituyente B, un grupo haloalquinil C₃₋₆-oxi, un R²⁰C(=O)- (en donde R²⁰ representa un grupo alquilo C₁₋₆, un grupo haloalquilo C₁₋₆, un grupo cicloalquilo C₃₋₈, un grupo alcoxi C₁₋₆, un grupo haloalcoxi C₁₋₆, un grupo cicloalcoxi C₃₋₈ o un R²¹R²²N- (en donde R²¹ y R²² representan cada uno, de modo independiente, un átomo de hidrógeno, un grupo alquilo C₁₋₆ opcionalmente sustituido con el sustituyente B¹, un grupo haloalquilo C₁₋₆ o un grupo cicloalquilo C₃₋₈ o R²¹ y R²² en combinación con el átomo de nitrógeno al que están unidos forman un grupo aziridinilo, un grupo azetidinilo, un grupo pirrolidinilo, un grupo piperidinilo, un grupo homopiperidinilo o un grupo azocanilo)), un R²⁰C(=O)O- (en donde R²⁰ es como se definió con anterioridad en la presente), un grupo de anillo de 3 a 6 miembros con contenido de 1 a 2 átomos de oxígeno, un R²³-L²- (en donde R²³ representa un grupo alquilo C₁₋₆ o un grupo haloalquilo C₁₋₆ y L² es S, SO o SO₂), un R²¹R²²N- (en donde R²¹ y R²² son como se definieron con anterioridad en la presente), o un R²⁴C(=O)N(R²⁵)- (en donde R²⁴ representa un átomo de hidrógeno, un grupo alquilo C₁₋₆, un grupo haloalquilo C₁₋₆, un grupo cicloalquilo C₃₋₈, un grupo alcoxi C₁₋₆, un grupo haloalcoxi C₁₋₆, un grupo cicloalcoxi C₃₋₈ o un R²¹R²²N- (en donde R²¹ y R²² son como se definieron con anterioridad en la presente) y R²⁵ representa un átomo de hidrógeno, un grupo alquilo C₁₋₆ opcionalmente sustituido con el sustituyente B¹, un grupo haloalquilo C₁₋₆ o un grupo cicloalquilo C₃₋₈); R³ representa un átomo de hidrógeno, un átomo de halógeno, un grupo nitro, un grupo alquilo C₁₋₆ opcionalmente sustituido con el sustituyente C, un grupo haloalquilo C₁₋₆, un grupo cicloalquilo C₃₋₈ opcionalmente sustituido con el sustituyente C, un grupo alcoxi C₁₋₆ opcionalmente sustituido con el sustituyente C, un grupo haloalcoxi C₁₋₆, un grupo alquenilo C₂₋₆ opcionalmente sustituido con el sustituyente C, un grupo haloalquenilo C₂₋₆ un grupo alquinilo C₂₋₆ opcionalmente sustituido con el sustituyente C, un grupo haloalquinilo C₂₋₆, un R³⁰-L³- (en donde R³⁰ tiene la misma definición que R²³ y L³ tiene la misma definición que L²), un R³¹R³²N- (en donde R³¹ y R³² tienen la misma definición que R²¹ y R²²), o un R³³C(=O)- (en donde R³³ representa un grupo alquilo C₁₋₆ un grupo haloalquilo C₁₋₆ o un grupo cicloalquilo C₃₋₈); n representa un número entero de 0 a 5 (siempre que cuando n es 2 o más, los dos o más R² representen sustituyentes independientes); X representa un átomo de oxígeno o un átomo de azufre; Y representa un grupo fenilo, un grupo piridilo, un grupo piridazinilo, un grupo pirimidinilo, un grupo pirazinilo, un grupo triazinilo, un grupo tetrazinilo, un grupo tienilo, un grupo tiazolilo, un grupo isotiazolilo o un grupo tiadiazolilo, el grupo fenilo está sustituido con el sustituyente D en una posición orto y además está sustituido con 0 a 4 sustituyentes independientes D¹ de modo apropiado, el grupo piridilo, el grupo pirazinilo, el grupo pirimidinilo, el grupo piridazinilo, el grupo triazinilo o el grupo tetrazinilo está sustituido con el sustituyente D en una posición orto y además está sustituido con 0 a 3 sustituyentes independientes D¹ de modo apropiado, el grupo tienilo, el grupo tiazolilo, el grupo isotiazolilo o el grupo tiadiazolilo está sustituido con el sustituyente D en una posición orto y además está sustituido con 0 a 2 sustituyentes independientes D¹ de modo apropiado; el enlace con una línea de puntos indica un enlace doble o un enlace simple, el sustituyente A es al menos uno seleccionado del grupo que consiste en: un grupo hidroxi, un grupo ciano, un grupo cicloalquilo C₃₋₈, un grupo alcoxi C₁₋₆, un grupo haloalcoxi C₁₋₆, un grupo cicloalcoxi C₃₋₈, un R¹²R¹³N- (en donde R¹² y R¹³ representan cada uno, de modo independiente, un átomo de hidrógeno, un grupo alquilo C₁₋₆, un grupo haloalquilo C₁₋₆ o un grupo cicloalquilo C₃₋₈ o R¹² y R¹³ en combinación con el átomo de nitrógeno al que están unidos forman un grupo aziridinilo, un grupo azetidinilo, un grupo pirrolidinilo, un grupo piperidinilo, un grupo homopiperidinilo o un grupo azocanilo) y un R¹⁴-L¹- (en donde R¹⁴ representa un grupo alquilo C₁₋₆ o un grupo haloalquilo C₁₋₆ y L¹ representa S, SO o SO₂); el sustituyente B es al menos uno seleccionado del grupo que consiste en: un grupo hidroxi, un grupo ciano, un grupo cicloalquilo C₃₋₈, un grupo alcoxi C₁₋₆, un grupo haloalcoxi C₁₋₆, un grupo cicloalcoxi C₃₋₈, un grupo alcoxialcoxi C₂₋₆, un R²¹R²²N- (en donde R²¹ y R²² son como se definieron con anterioridad en la presente), un R²³-L²- (en donde R²³ y L² son como se definieron con anterioridad en la presente), un R²⁶R²⁷R²⁸Si- (en donde R²⁶, R²⁷ y R²⁸ representan cada uno, de modo independiente, un grupo alquilo C₁₋₆), un R²⁶R²⁷R²⁸Si-(CH₂)ₛ-O- (en donde s representa un número entero de 1 a 3 y R²⁶, R²⁷ y R²⁸ son como se definieron con anterioridad en la presente), un R²⁰C(=O)- (en donde R²⁰ es como se definió con anterioridad en la presente) y un grupo de anillo de 3 a 6 miembros con contenido de 1 a 2 átomos de oxígeno; el sustituyente B¹ es al menos uno seleccionado del grupo que consiste en: un grupo ciano, un grupo alcoxi C₁₋₆ un grupo haloalcoxi C₁₋₆ y un grupo cicloalcoxi C₃₋₈; el sustituyente C es al menos uno seleccionado del grupo que consiste en: un grupo hidroxi, un grupo ciano, un grupo cicloalquilo C₃₋₈, un grupo alcoxi C₁₋₆, un grupo haloalcoxi C₁₋₆, un grupo cicloalcoxi C₃₋₈, un R³¹R³²N- (en donde R³¹ y R³² tienen la misma definición que R²¹ y R²²) y un R³⁰-L³- (en donde R³⁰ tiene la misma definición que R¹⁴ y L³ tiene la misma definición que L¹); el sustituyente D es al menos uno seleccionado del grupo que consiste en: un átomo de halógeno, un grupo alquilo C₁₋₆, un grupo haloalquilo C₁₋₆, un grupo alcoxi C₁₋₆ y un grupo haloalcoxi C₁₋₆; y el sustituyente D¹ es al menos uno seleccionado del grupo que consiste en: un grupo hidroxi, un átomo de halógeno, un grupo alquilo C₁₋₆, un grupo haloalquilo C₁₋₆, un grupo cicloalquilo C₃₋₈, un grupo alcoxi C₁₋₆, un grupo haloalcoxi C₁₋₆ y un grupo cicloalcoxi C₃₋₈.]Claim 1: A compound represented by the formula (1) or a salt thereof, [characterized in that R¹ represents a hydroxy group, a cyano group, a C₁₋₆ alkyl group optionally substituted with substituent A, a C₁₋₆ haloalkyl group , a C₃₋₈ cycloalkyl group optionally substituted with substituent A, a C₂₋₆ alkenyl group optionally substituted with substituent A, a C₂₋₆ haloalkenyl group, a C₂₋₆ alkynyl group optionally substituted with substituent A, a haloalkynyl group C₂₋₆, a C₁₋₆ alkoxy group optionally substituted with substituent A, a C₁₋₆ haloalkoxy group, a C₃₋₈ cycloalkoxy group optionally substituted with substituent A, C₂₋₆-oxy alkenyl group optionally substituted with substituent A , a C₂₋₆-oxy haloalkenyl group, a C₃₋₆-oxy alkynyl group optionally substituted with substituent A, a C₃₋₆-oxy haloalkynyl group, or an R ⁰R¹¹N- (where R¹⁰ and R¹¹ in each represent, independently, a hydrogen atom or an alkyl C₁₋₆); R² represents a halogen atom, a hydroxy group, a cyano group, a nitro group, a C₁₋₆ alkyl group optionally substituted with the substituent B, a C₁₋₆ haloalkyl group, a C₃₋₈ cycloalkyl group optionally substituted with the substituent B, a C₂₋₆ alkenyl group optionally substituted with substituent B, a C₂₋₆ haloalkenyl group, a C₂₋₆ alkynyl group optionally substituted with substituent B, a C₂₋₆ haloalkynyl group, an optionally substituted C₁₋₆ alkoxy group with substituent B, a C₁₋₆ haloalkoxy group, a C₃₋₈ cycloalkoxy group optionally substituted with substituent B, a C₂₋₆-oxy alkenyl group optionally substituted with substituent B, a C₂₋₆-oxy haloalkenyl group, a C₃₋₆-oxy alkynyl group optionally substituted with substituent B, a C₃₋₆-oxy haloalkynyl group, a R²⁰C (= O) - (where R²⁰ represents a C₁₋ alkyl group , a C₁₋₆ haloalkyl group, a C₃₋₈ cycloalkyl group, a C₁₋₆ alkoxy group, a C₁₋₆ haloalkoxy group, a C₃₋₈ cycloalkoxy group or an R²¹R²²N- (where R²¹ and R²² each represent, of independently, a hydrogen atom, a C₁₋₆ alkyl group optionally substituted with the substituent B¹, a C₁₋₆ haloalkyl group or a C₃₋₈ or R²¹ and R²² cycloalkyl group in combination with the nitrogen atom to which they are attached form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group or an azocanyl group)), an R²⁰C (= O) O- (where R²⁰ is as defined hereinbefore), a 3 to 6 member ring group containing 1 to 2 oxygen atoms, a R²³-L²- (where R²³ represents a C₁₋₆ alkyl group or a C₁₋₆ haloalkyl group and L² is S, SO or SO₂) , an R²¹R²²N- (where R²¹ and R²² are as defined were previously initiated herein), or an R²⁴C (= O) N (R²⁵) - (where R²⁴ represents a hydrogen atom, a C₁₋₆ alkyl group, a C₁₋₆ haloalkyl group, a C₃₋₈ cycloalkyl group , a C₁₋₆ alkoxy group, a C₁₋₆ haloalkoxy group, a C₃₋₈ cycloalkoxy group or an R²¹R²²N- (where R²¹ and R²² are as defined hereinbefore) and R²⁵ represents a hydrogen atom, a C₁₋₆ alkyl group optionally substituted with the substituent B¹, a C₁₋₆ haloalkyl group or a C₃₋₈ cycloalkyl group); R³ represents a hydrogen atom, a halogen atom, a nitro group, a C₁₋₆ alkyl group optionally substituted with the C substituent, a C₁₋₆ haloalkyl group, a C₃₋₈ cycloalkyl group optionally substituted with the C substituent, a C₁₋₆ alkoxy group optionally substituted with substituent C, a C₁₋₆ haloalkoxy group, a C₂₋₆ alkenyl group optionally substituted with substituent C, a C₂₋₆ haloalkenyl group, a C₂₋₆ alkynyl group optionally substituted with substituent C , a haloalkynyl group C₂₋₆, a R³⁰-L³- (where R³⁰ has the same definition as R²³ and L³ has the same definition as L²), a R³¹R³²N- (where R³¹ and R³² have the same definition as R²¹ and R²² ), or an R³³C (= O) - (where R³³ represents a C₁₋₆ alkyl group, a C₁₋₆ haloalkyl group or a C₃₋₈ cycloalkyl group); n represents an integer from 0 to 5 (provided that when n is 2 or more, the two or more R² represent independent substituents); X represents an oxygen atom or a sulfur atom; And it represents a phenyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, a tetrazinyl group, a thienyl group, a thiazolyl group, an isothiazolyl group or a thiadiazolyl group, the phenyl group is substituted with the substituent D in an ortho position and in addition it is substituted with 0 to 4 independent substituents D¹ appropriately, the pyridyl group, the pyrazinyl group, the pyrimidinyl group, the pyridazinyl group, the triazinyl group or the tetrazinyl group is substituted with substituent D in an ortho position and in addition is substituted with 0 to 3 independent substituents D¹ appropriately, the thienyl group, the thiazolyl group, the isothiazolyl group or the thiadiazolyl group is substituted with the substituent D in an ortho position and is substituted with 0 to 2 independent substituents D¹ appropriately; the link with a dotted line indicates a double bond or a single bond, the substituent A is at least one selected from the group consisting of: a hydroxy group, a cyano group, a C₃₋₈ cycloalkyl group, a C₁₋ alkoxy group ₆, a C₁₋₆ haloalkoxy group, a C₃₋₈ cycloalkoxy group, a R¹²R¹³N- (where R¹² and R¹³ each independently represent a hydrogen atom, a C₁₋₆ alkyl group, a C₁₋ haloalkyl group ₆ or a C₃₋₈ or R¹² and R¹³ cycloalkyl group in combination with the nitrogen atom to which they are attached form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group or an azocanyl group) and a R¹⁴-L¹- (where R¹⁴ represents a C₁₋₆ alkyl group or a C₁₋₆ haloalkyl group and L¹ represents S, SO or SO₂); the substituent B is at least one selected from the group consisting of: a hydroxy group, a cyano group, a C₃₋₈ cycloalkyl group, a C₁₋₆ alkoxy group, a C₁₋₆ haloalkoxy group, a C₃₋₈ cycloalkoxy group, an alkoxyalkoxy group C₂₋₆, an R²¹R²²N- (where R²¹ and R²² are as defined hereinbefore), an R²³-L²- (where R²³ and L² are as defined hereinbefore), a R²⁶R²⁷R²⁸Si- (where R²⁶, R²⁷ and R²⁸ each independently represent a C alquilo alkyl group), a R²⁶R²⁷R²⁸Si- (CH₂) ₛ-O- (where s represents an integer from 1 to 3 and R²⁶ , R²⁷ and R²⁸ are as defined hereinbefore), an R²⁰C (= O) - (where R²⁰ is as defined hereinbefore) and a 3 to 6 member ring group containing 1 at 2 oxygen atoms; the substituent B¹ is at least one selected from the group consisting of: a cyano group, a C alco alkoxy group, a C₁₋₆ haloalkoxy group and a C₃₋₈ cycloalkoxy group; the substituent C is at least one selected from the group consisting of: a hydroxy group, a cyano group, a C₃₋₈ cycloalkyl group, a C₁₋₆ alkoxy group, a C₁₋₆ haloalkoxy group, a C₃₋₈ cycloalkoxy group, a R³¹R³²N- (where R³¹ and R³² have the same definition as R²¹ and R²²) and a R³⁰-L³- (where R³⁰ has the same definition as R¹⁴ and L³ has the same definition as L¹); the substituent D is at least one selected from the group consisting of: a halogen atom, a C₁₋₆ alkyl group, a C₁₋₆ haloalkyl group, a C₁₋₆ alkoxy group and a C₁₋₆ haloalkoxy group; and the substituent D¹ is at least one selected from the group consisting of: a hydroxy group, a halogen atom, a C₁₋₆ alkyl group, a C₁₋₆ haloalkyl group, a C₃₋₈ cycloalkyl group, a C₁₋ alkoxy group ₆, a C₁₋₆ haloalkoxy group and a C₃₋₈ cycloalkoxy group.]

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